23-O-Acetylshengmanol-3-o-alpha-L-arabinoside

Base Information

• Chemical Name: 23-O-Acetylshengmanol-3-o-alpha-L-arabinoside
• CAS No.: 402513-88-6
• Molecular Formula: C37H58O10
• Molecular Weight: 662.85042
• UNII: 408998370C
• Nikkaji Number: J1.648.087H
• Wikidata: Q27258304
• Mol file: 402513-88-6.mol

Synonyms:402513-88-6;Acetylcimigenol arabinoside;23-O-Acetylshengmanol-3-o-alpha-L-arabinoside;Acetylshengmanol arabinoside;Acetylcimigenol-3-O-alpha-L-arabinopyranside;Acetylcimigenol 3-O-alpha-L-arabinopyranside;UNII-408998370C;23-O-Acetylshengmanol-3-o-alpha-L-arabinoside, (-)-;408998370C;9,19-Cyclolanostan-16-one, 23-(acetyloxy)-3-(alpha-L-arabinopyranosyloxy)-24,25-epoxy-15-hydroxy-, (3beta,15alpha,23R,24S)-;(3beta,15alpha,23R,24S)-23-(acetyloxy)-3-(alpha-L-arabinopyranosyloxy)-24,25-epoxy-15-hydroxy-9,19-cyclolanostan-16-one;Acetylcimigenol3-O-alpha-L-arabinopyranside;[(1R,3R)-1-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(1S,3R,6S,8R,11R,12S,13R,15R,16R)-13-hydroxy-7,7,12,16-tetramethyl-14-oxo-6-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]butyl] acetate;HY-N2170;AKOS037514912;Acetylcimigenol 3-O-alpha-L-arabinopyran;MS-31026;CS-0019479;Q27258304;23-O-ACETYLSHENGMANOL-3-O-.ALPHA.-L-ARABINOSIDE;23-O-ACETYLSHENGMANOL-3-O-.ALPHA.-L-ARABINOSIDE, (-)-;(23R,24S)-3beta-(alpha-L-Arabinopyranosyloxy)-16-oxo-23-acetoxy-24,25-epoxy-9beta,19-cyclolanostane-15alpha-ol;9,19-CYCLOLANOSTAN-16-ONE, 23-(ACETYLOXY)-3-(.ALPHA.-L-ARABINOPYRANOSYLOXY)-24,25-EPOXY-15-HYDROXY-, (3.BETA.,15.ALPHA.,23R,24S)-

Chemical Property of 23-O-Acetylshengmanol-3-o-alpha-L-arabinoside

Chemical Property:

• Boiling Point: 748.5±60.0 °C(Predicted)
• PKA: 12.90±0.70(Predicted)
• PSA: 155.28000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 3.53480
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 662.40299804
• Heavy Atom Count: 47
• Complexity: 1300

Purity/Quality:

99%, ^*data from raw suppliers

Acetylcimigenol arabinoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(C1C(O1)(C)C)OC(=O)C)C2C(=O)C(C3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)C)OC7C(C(C(CO7)O)O)O)C)C)O
• Isomeric SMILES: C[C@H](C[C@H]([C@H]1C(O1)(C)C)OC(=O)C)[C@H]2C(=O)[C@@H]([C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)C)C)O
• Uses: Acetylcimigenol Arabinoside is a cytotoxic agent against human oral squamous cell carcinoma cells and normal human gingival fibroblasts.

Technology Process of 23-O-Acetylshengmanol-3-o-alpha-L-arabinoside

There total 3 articles about 23-O-Acetylshengmanol-3-o-alpha-L-arabinoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C39H60O11 (1316305-74-4) → 23-O-acetylshengmanol 3-O-α-L-arabinopyranoside (402513-88-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/j.phytochem.2011.03.022

Reference yield:

25-O-acetylcimigenol 3-O-β-D-glucopyranosyl-(1<*>3)-β-D-xylopyranoside → 23-O-acetylshengmanol 3-O-β-D-xylopyranoside (402513-88-6)

Guidance literature:

With acetic acid; In water; for 96h; Ambient temperature; Cellulase A 3 (from Aspergillus niger);

DOI:10.1248/cpb.42.1940

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 23-O-acetylshengmanol 3-O-(2'-O-malonyl)-β-D-xylopyranoside → 23-O-acetylshengmanol 3-O-β-D-xylopyranoside (402513-88-6) + malonic acid 2-{17-[3-acetoxy-3-(3,3-dimethyl-oxiranyl)-1-methyl-propyl]-15-hydroxy-4,4,13,14-tetramethyl-16-oxo-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yloxy}-4,5-dihydroxy-tetrahydro-pyran-3-yl ester methyl ester

Guidance literature:

In methanol; diethyl ether;

DOI:10.1248/cpb.47.1175

upstream raw materials:

diazomethane

C₃₉H₆₀O₁₁

Refernces

• 1、 Kusano, Akiko,Shibano, Makio,Kusano, Genjiro. "Studies on the constituents of Cimicifuga species. XXVII. Malonyl cyclolanostanol glycosides from the underground parts of Cimicifuga simplex Wormsk". . p. 1175 - 1179. Retrieved 1999.